In lab, we did an oxidation of 2-ethyl-1, 3-hexanediol with acetic acid and sodium hydrochlorite. I understand the acid is the solvent and in combination with NaOCl produces hypochlorous acid the oxidizing agent. Then we mix with an ice salt mixture and then extract with ether before washing with sodium carbonate and sodium hydroxide. The part that confuses me is the washing. Both sodium carbonate and sodium hydroxide are neutralizers so why are both used? Wouldn't once suffice?

Is the product an aldehyde or an acid? Which washing do you do first?

NaHCO3 is used generally to form the sodium salt of strong acid like carboxylic acids while NaOH forms salts with both strong and weak; i.e., phenols as well as carboxylic acids.

The product was an ketone with the primary alcohol remaining. And the sodium carbonate was used to wash first then the sodium hydroxide.

The purpose of using both sodium carbonate and sodium hydroxide for washing in this oxidation reaction is to ensure the complete removal of any acidic impurities and to neutralize the reaction mixture.

Sodium carbonate (Na2CO3) is used as a first wash to remove any remaining acetic acid, which is a weak acid. Acetic acid is soluble in water, and by washing with sodium carbonate solution, any remaining acetic acid will react with sodium carbonate to form sodium acetate (a salt) and carbon dioxide gas. This reaction helps remove the acetic acid from the organic layer.

On the other hand, sodium hydroxide (NaOH), which is a strong base, is used as a second wash to neutralize any remaining acidic impurities, such as hypochlorous acid (formed from the reaction of acetic acid and sodium hypochlorite). Sodium hydroxide reacts with acidic impurities to form sodium salts, water, and carbon dioxide gas, which can be easily removed.

By using both sodium carbonate and sodium hydroxide for washing, any remaining acidity in the reaction mixture can be effectively neutralized, ensuring the removal of acidic impurities and achieving a neutral or slightly basic final product.

The process you described involves several steps, including the oxidation of 2-ethyl-1, 3-hexanediol and subsequent washing with sodium carbonate and sodium hydroxide. Let me explain the purpose of each step and why both sodium carbonate and sodium hydroxide are used for washing.

First, let's understand the overall reaction of the oxidation process. In this reaction, acetic acid serves as the solvent and reacts with sodium hypochlorite (NaOCl) to produce hypochlorous acid (HOCl) which acts as the oxidizing agent. This hypochlorous acid is then used to oxidize the 2-ethyl-1,3-hexanediol.

After the oxidation reaction, the mixture is typically cooled by using an ice salt mixture to promote the formation of solid precipitates. These precipitates are often impurities that can be removed by extraction.

The extraction step involves using a nonpolar solvent such as ether to separate the organic (nonpolar) phase from the aqueous (polar) phase. This helps to isolate the desired organic compounds, while leaving behind most of the impurities in the aqueous layer.

Now, let's focus on the washing step after the extraction. Both sodium carbonate (Na2CO3) and sodium hydroxide (NaOH) are used as washing agents, but they serve different purposes.

Sodium carbonate is primarily used to remove acidic impurities. It reacts with acidic compounds (such as unreacted acetic acid or by-products of the oxidation) to form water-soluble salts, which can be easily removed during the washing. This process is commonly referred to as "neutralization" because the acidic impurities are neutralized by the basic sodium carbonate.

On the other hand, sodium hydroxide is used to remove any remaining acidic impurities that were not effectively neutralized by sodium carbonate. Sodium hydroxide is a stronger base compared to sodium carbonate, and it can react with more acidic impurities that might still be present. This helps to ensure that the final product is free from any residual acidic contaminants.

In summary, both sodium carbonate and sodium hydroxide are used for washing to effectively remove acidic impurities. Sodium carbonate helps neutralize the acidic contaminants, while sodium hydroxide provides additional cleaning to ensure that all acidic impurities are eliminated.